


the doctor is in (put flowers in your cannons)

by persimonne



Category: Star Wars Sequel Trilogy
Genre: Age Difference, Alternate Universe - Modern Setting, Anal, Anal Fingering, Anal Play, Anal Plug, Anal Sex, Anal Training, Barebacking, Bisexual Kylo Ren, Body Part Kinks, Butt Plugs, Chatting & Messaging, Clit Play, Clit Stimulation, Dirty Talk, Enthusiastic Consent, Exhibitionism, F/M, Falling In Love, Fluff, Fluff and Smut, Kylo fucks Rey's ass, Kyluxma, Masturbation, Meet-Cute, Needy Rey, Oral Sex, Other Ships Not Mentioned in Tags, PWP without Porn, Phaslo - Freeform, Rey wants her anal V-card gone asap, Rimming, Safe Sane and Consensual, Sex Talk, Shylo Ren, Voyeurism, ass pics, finnrose - Freeform, pussy pics, seriously it's a butt fic, straight to the A, vaginal sex not contemplated
Language: English
Status: Completed
Published: 2018-05-03
Updated: 2018-05-03
Packaged: 2019-05-01 14:56:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,526
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14523111
Author URL: https://archiveofourown.org/users/persimonne/pseuds/persimonne
Summary: Rey needs a teacher to coach her in anal stuff and she meets butt expert Kylo Ren.





	the doctor is in (put flowers in your cannons)

**Author's Note:**

> Mainly following this prompt at reylohardkinks.tumblr.com: 
> 
> "Anal!Only kink. Rey gets curious about anal sex and looks for a teacher on *website of your choice* because she doesn't want her experience to end up badly. She meets Kylo and they agree to try it. She loves it so much that they begin to meet regularly just for anal sex (no oral or vaginal penetration please, tongue/fingers on Rey more than welcome)."
> 
> What it says on the label, but with more puns, fluff and random kinks!  
> It can be a Dead Dove situation, so, step back if you think Rey shouldn't take Kylo's cock up her ass.
> 
> Many thanks to my precious beta, thewayofthetrashcompactor (BriarLily).

“... and then I came again, when he finally fucked my ass!”, Rose giggled.

 

Rey’s eyebrows flew up to her hairline.

 

“Don’t make that face, Rey! It’s 2018 and it wasn’t even our first time. We tried a bunch of times before and finally yesterday I came from it! Finn was so hard that he came just a few seconds after me.” She smiled, sipping her tea.

 

Rey felt a bit uneasy at the thought but she could clearly feel her heartbeat speeding up. “I had no idea women could come like that?”

 

-

 

Rey truly didn’t have the slightest idea.

 

She was used to other women sharing their horrible experiences about anal sex, and now here her friend was acting like it was the best time of her life. Rey had always dismissed it as something uncomfortable and humiliating, not the kind of thing she associated with Finn, one of the sweetest guys she knew. Finn was a good guy, and good guys didn’t stuck their dicks in good girls’ butts, did they?

 

Rose’s words woke something inside Rey, and she couldn’t stop thinking about what her friend revealed her. She felt curiosity and shame at the same time, and the supposed wrongness of the topic made her heart jump in her chest and her pussy clench in guilty interest.

 

That evening, she browsed the net for more information: she desperately wanted to understand if Rose’s experience was indeed exceptional or if could be more or less normal.

 

After the thousandth porn site, and many useless pseudo-kink forums, she finally stumbled on an e-book: “The Joys of the Backdoor”. The author was a person going by the most ridiculous nickname: Kylo Ren.

Clicking on the link, she sadly discovered that it wasn’t available anymore; however, looking back at the webpage, she found an e-mail address at the very bottom.

 

“Great. Now I have to write to that asshole about his book about assholes.”

 

She opened a new message and typed:

 

_Dear Mr. Ren,_

_I would like to purchase your ebook but the link doesn’t seem to work anymore. Could you send me a working link, please?_

 

_Rey_

 

She closed her laptop and headed to bed, trying not to think about why she was slowly becoming obsessed.

 

The following morning, her phone buzzed during class: Kylo Ren had replied her email.

 

_Hi Rey,_

_I’m so sorry to tell you that the ebook is no more available. I wrote it with my ex wife, and she decided to remove it from the site after we divorced._

_I may have a paper copy somewhere, and I could ship it to you, if that’s okay? Are you of age?_

_Were you interested in the whole book or just some section in particular? It’s almost 200 pages and shipping rates are not cheap._

 

_Let me know,_

 

_Kylo_

 

Rey covered her phone, hoping that no one was looking at what she was reading. She typed her answer very quickly, before losing all her courage:

 

_Kylo,_

_Thank you for your kind offer. Actually I have no idea what to expect from your book, I was just curious about anal sex? I’m a total newbie and yes, I’m of age._

 

_Rey_

 

She kept checking her phone during class. It finally buzzed again during her lunch break, making her heart almost skip a beat.

 

_Rey,_

_The book is mainly a guide about how to engage in anal outercourse and intercourse, from different points of view: passive and active male, passive and active (pegging) female, and there are also tips about how to do it alone._

_I can send you just the parts you require the most,maybe. I won’t ask for money, just cover the shipping fees and please, don’t divulge this print anywhere (or my attorney will kill me)._

_Let me also know your address (you can use a P.O. box if you’re uncomfortable), I will prepare a simple envelope._

 

_Kylo_

 

Rey’s interest was definitely piqued. A whole guide? Female perspective on the act and pegging too? This seemed almost too good to be true.

 

_Kylo,_

_I’m interested in the whole thing, I will cover the entire shipping, don’t worry._

_My P.O. box address is…_

 

This guy seemed very professional so far; the reviews about his book were very good and she couldn’t wait to read the whole guide. If he wrote a personal point of view about pegging that could only mean that he experienced being on the receiving end too, unlike all the crusty boys she knew, always jerking to porn and demanding sex from their girlfriends without even managing to satisfy them.

 

Kylo didn’t answer until the evening:

 

_Rey,_

_Great news! I managed to find the whole book. Sadly, that means there are a lot of loose pages because we never meant to sell physical copies. I’ve prepared a parcel with everything inside._

_More good news, no need to pay for anything! Your post office is not far from where I work, so I will just leave your parcel at the coffee shop at the corner tomorrow morning. It’s a brown package with your name on it._

_Just let me know what you think about the book. Maybe leave a review when the e-book will be online again (we’re working hard for that to happen asap)._

 

_Kylo_

 

Rey couldn’t believe her eyes. Not only did she and this Kylo lived in the same city, but they frequented the same places too: she’d stopped for breakfast in that coffee shop many times before her classes.

 

In the morning, she went there early and took seat in a corner, pretending to read her assignments but keeping her eyes on the door. Her heart was beating wildly in her chest and she kept tapping the floor with her foot.

 

She was dying to see Kylo in person. She wanted to associate a face with the man that loved anal sex so much to write a complete guide about doing it right. She was so distracted that she almost missed the tall man entering the shop. Luckily, she managed to catch him talking to a waiter before he could hastily exit.

 

“... leave this parcel here? It’s for a girl named Rey, she should come soon. Please be careful, it’s an out of edition book, don’t lose it.”

 

Holy shit! She didn’t manage to see his face, but he was very tall, very broad, and he had a lovely voice… and he also seemed kinda shy? She could hardly believe that a man who'd published a two hundred page manual on anal sex could be _shy_.

 

After retrieving the parcel, she followed her classes without real interest: her thoughts kept wandering on a tall dark stranger.

 

A tall dark stranger writhing in front of her, stretched around a strap on dildo.

 

A tall dark stranger filling her ass with his cock and whispering filthy words in her ear.

 

After her lessons, Rey literally ran home. Finn was working at his evening job, and she closed her bedroom door, eager to unpack the brown paper parcel. There was her name written on it, in beautiful calligraphy. She carefully folded the sheet and closed it in her desk drawer. She finally brought the unbound book to her bed and begun reading the introduction.

 

Ren and his now ex-wife (nicknamed Mrs. Phasma) were both doctors, and they met at uni. They begun regularly having anal sex early on in their relationship because she loved it and he always wanted to try it, and after a few years of marriage they also included another man (going by the laughable name of Hux) in their experiments.

 

Rey clenched her thighs at the mental image of Kylo being fucked by another man. She knew anal sex between two men could be pleasurable and she began feeling incredibly hot all over just thinking about it and trying to imagine Kylo’s broad body engaging in such raunchy activities with another faceless male.

 

But the most surprising and erotic part was the one explaining that Ren and his wife sometimes indulged in whole weekends solely dedicated to anal sex.

Whole weekends.

And they loved it. They used it like a treat of sorts, like a reward, like a special cuddle between them.

 

She tried to imagine herself pampered in that extremely humiliating way. This was absolutely wrong, and debasing, and she burned to try it.

She exhaled heavily:

 

“Great, I’m soaked after just reading two pages. What’s wrong with me?”.

 

After the introduction, there was a paragraph saying that anal sex wasn’t for everyone and to stop at the first signal of discomfort. This somehow calmed Rey: the book was written by health professionals after all, surely they knew what they were talking about and therefore anal if done well could be nothing dangerous.

 

She devoured the first part, which was all about anatomy: apparently her anus was full of nerves even if she was not equipped with a prostate, and many women could come from this kind of stimulation. Mrs. Phasma then recommended to engage in anal intercouse right after an orgasm, “to be more relaxed”, and after attentive preparation. She couldn’t help wondering if her husband was so attentive to make her always come at least once before fucking her ass. Reading the parts written by him, he seemed totally devoted to his wife’s needs.

 

She blushed wildly discovering a whole chapter about enemas and she skipped it hastily. That felt even more embarrassing than anal itself. Maybe she could ask Kylo about that uncomfortable topic later.

 

The following part was about plugs and how to use them. Her heart galloped just reading the title: _Anal Training._ The mere thought of daily debasing herself towards the final goal of letting a cock glide smoothly into her anus rendered her breathless and bewildered. This was beyond the intimacy of letting another person fuck her ass. This was consciously and purposefully setting a whole routine around her butt.

 

Cherry on top, apparently Kylo loved to be plugged too, in particular while penetrating his wife or that other guy, or just staying home relaxing. He really was something else.

 

Rey had so many questions for him! She took her phone in her hand and started typing an email:

 

_Kylo,_

_I’m readying the book and I have questions. Can I bother you?_

 

_Rey_

 

He answered after a few second:

 

_Sure, I’m on a train and I’m free tonight. Here’s my number…_

 

Rey saved it and set a new chat with the title: _Butt Doctor_

He sent a laughing emoji straight away and she smiled.

 

_K: How’s the book so far?_

 

_R: Great? I’m sorry I have so many questions but I’m really new to this._

 

_K: Don’t worry, I was a newbie too before meeting my ex wife, she’s the real expert of the two. I was just desperate to try it and she educated me on the topic._

 

Rey felt her face become crimson before typing:

 

_R: Okay… I already know it can be painful the first few times but I’m not worried about that… I’m more worried about other things like… will I have to have an enema before having sex? My friend didn’t mention it and this worries me a bit?_

 

_K: Not really, if you’re regular you can skip it. Just use a lot of lube and it will be okay. About the pain, it really lasts few seconds if done right._

 

_R: Thanks! And what about plugs?_

 

_K: You can buy a set online and begin wearing them a little every day, from the smallest to the biggest one. But you have to proceed carefully with this. The slower, the better._

 

Rey had never felt wetter in her life. Kylo kept giving her serious and professional tips, and she’d almost soaked her bed at the thought of wearing a different plug everyday. For herself, but for someone else’s pleasure too. This anal training idea was literally wrecking her.

 

_K: Please Rey, remember that anal sex is not compulsory and you have to think about your health first! Is anyone pressuring you to do it?_

 

_R: No, it’s not like that. I don’t even have a boyfriend._

 

_K: Never have anal sex because someone is forcing you. It can lead to serious discomfort and even injuries._

 

_R: It’s just that I discovered that a close friend of mine does it and she also enjoys it and I got curious._

 

_K: Great for her! You can begin experimenting alone but please, promise me that you will stop if you feel the slightest discomfort. I’ll send you a link where you can buy plugs. I’m here If you have more questions._

 

Rey finished the book after a few days, trying and often failing not to think all day long about the parts that tickled her interest the most. She bookmarked or underlined whole sentences or paragraphs to read again later. Kylo and his ex-wife’s games were certainly very interesting and unusual (at least for her), and she was slowly discovering that she wanted to try pretty much everything.

 

Her favourite part was in a chapter about the best positions for anal sex. Kylo’s favourites were the ones where he could still keep an eye on his partner’s pussy, “because vulvae are the best and I could watch them all day long”. She’d never thought about her pussy as something beautiful. Her ex-boyfriend never looked at her like that; he just stuck his dick in her, always making the same movement. She had to explicitly ask for oral sex or he wouldn’t even lick her. Boring.

 

She also ordered a set of soft plugs from the site suggested by Kylo. She touched herself daily thinking about his voice whispering to her which plug to wear, and imagining him looking at her empty pussy while fucking her. The fantasy was thrilling beyond salvation.

One night, after playing with her clit and reaching a fantastic orgasm, she crouched on the floor and, after collecting moisture around her inner labia, she breached her anus with a fingertip.

 

“Oh!”

 

It definitely wasn’t painful nor unpleasant. The little hairs on her arms stood up until she extracted her finger. She then inserted another finger alongside the first one and it started burning a little, but nothing dramatic. She couldn’t wait to try her plugs set.

 

She waited for the end of her exams session to finally unpack and clean the set. Totally relaxed after a warm shower, she inserted the littlest plug of the six, after applying a generous amount of lube. It was a just little bit bigger that two of her fingers together and, after stinging for a second or two, it entered without too much fuss.

 

She exhaled, enjoying the new and strange sensation. It wasn’t painful at all and she clearly felt its length in her bowels. She felt her body hair stand up and her clit getting hard, and thought about letting Kylo know that she was trying her first plug.

 

_R: I’m wearing the smaller plug of the set. I like the sensation even if it’s a bit strange? I was thinking about touching myself and removing it after I come. What do you think? ;)_

 

_K: I think you can find all the informations about plugs in the book. You can keep it until you’re comfortable but for the first time don’t overindulge._

 

Rey almost felt hurt by his harsh tone.

 

_R: I’m sorry, I didn’t want to bother you. I just thought that it would have been easier not being completely alone in this? I will follow the book instructions without bothering you further._

 

She closed the phone and got up to remove the plug. She didn’t feel at ease continuing anymore.

 

Just before entering the bathroom, her phone rang, and she recognized the sound for a voice message. It was a real voice message, from him! She tapped on the icon with trembling fingers.

 

There was background noise, and finally his beautiful voice:

 

“Rey, I didn’t want to upset you… It’s just that I don’t understand if you really just want instructions for this or you w-want something more? I’m a bit slow sometimes reading people, I’ve had a stressful day and it’s not easy to catch nuances in written communication? You seem kinda f-flirty? If you’re interested we can chat this evening; right now I have to come back to my meeting. L-let me know, okay?”

 

Rey listened to his message twice before replying:

 

_R: Okay, tell me when you’ll be free this evening._

 

After having dinner with Finn, she told him she had to phone a counselor for a personal project and went to her room. Kylo’s message was waiting for her:

 

_K: I’m home now, finally free from those assholes ;)_

 

She decided to skip the written communication and to phone him. He answered, seeming flustered.

 

“Rey?”

 

“That’s me. I decided to phone you because it’s faster. I would like to be coached in this anal thing by you because I find it exciting and I already touched myself thinking about it a lot of times.” She all but blurted all of this out, trying to keep her voice low in case Finn was listening.

 

Kylo didn’t respond for a few seconds, but Rey could feel him wheezing on the other end.

 

“A-are you sure Rey? This is a bit different that meeting someone and then d-deciding to have sex with them, you know? You don’t even know how old I am!”

 

“You can’t be so old, come on. And age is totally meaningless if we keep playing by phone. I’m not a virgin, just single and horny and I want to try new stuff. Please, think about it. I’m becoming obsessed with this anal thing… everyone kept telling me that’s it’s dirty and wrong and no sane woman would enjoy it but I’m here, thinking about being stuffed down there. How’s that? I need a teacher. Are you in?”

 

Kylo was silent for a moment, and Rey waited anxiously. He'd written an anal sex guide, coaching her by phone would be nothing in comparison. Right? Her heart beat in anticipation. She wondered if he was hard, then shoved the thought aside.

 

“O-okay…w-would you like to begin right now?”

 

Rey had never had as much fun as that week. Every day, they chatted a bit on the phone, getting to know each other better. She discovered that he was ten years her senior, that Kylo wasn’t his real name, that he was indeed a real doctor, and astoundingly his hobby (save for stuffing his and other people’s butts) was calligraphy. And he sadly considered himself ugly.

 

He had a private studio not far from her neighbourhood but he lived in the countryside. His ex-wife had had a brief fling with that butt guy Hux without telling him and they parted ways after that. They decided to write the book after the umpteenth patient requesting help to remove something from their anuses.

 

She told him that she was twenty-one and was studying at uni with a scholarship because she was the best in her mechanic course. She’d only had one boyfriend between high school and uni but they split after a few months. He wasn’t great in the bedroom and he never managed to make her come during sex. She never thought about anal as something pleasurable for women, and now the mere thought of the act was literally consuming her.

 

They both couldn’t wait to unwind a bit together, after a long day of work and study. He really was the shyest man ever but seemed very enthusiastic about coaching her, after opening up a bit.

 

That week, she kept using the smallest plug for a at least fifteen minutes almost every evening, but didn’t manage to come with the toy inserted. She got very wet just thinking about it, but no orgasms. The book confirmed that it wasn’t unusual, and that there were two possible solutions: to stop trying altogether or to avoid masturbating without the plug inserted for a while to see what could happen. Rey obviously chose the latter of the two options.

 

The second week after that fateful phone call, she requested a series of voice messages with instructions:

 

_R: I need you to order me around a bit. I want you to instruct me clearly about what to do with my ass. You think you can handle that?_

 

He recorded himself for her, trying to keep his voice firm and commanding, telling her what buttplug to insert, how to do it and how much time to keep it. Rey was shocked to find that he was new to this kind of play with dirty talk, although she supposed it was an unusual situation. He certainly did it well, but she still got the impression that he was trying to overcome that worry about their ages he'd mentioned when they first started talking, like he felt he was taking advantage of her.

 

She kept using the smallest two plugs of the set and built up to trying to wear one of those every evening for at least thirty minutes. Touching herself exclusively while using the plug was far from unpleasant but it still left her horny as hell and unsatisfied, even listening to the detailed instructions Kylo recorded for her.

 

 _R: It seems this isn’t going anywhere._ _I still feel the plug like an intrusion I think? It seems I can’t come with something in my body, but you wrote on the book that it can happen._

 

_K: The first time I used a plug I was receiving a blowjob and I came like a train, but I guess that’s thanks to my prostate. Do you manage to come easily otherwise?_

 

_R: I have no problem while touching my clit, but I never came having sex with another person._

 

_K: I will call you tonight. We’ll find a solution, I promise._

 

That evening, after a few tries, Rey managed to insert the third plug from the set. She immediately told him.

 

_R: Medium one in. Are you home?_

 

After a few minutes, her phone rang.

 

“Hey, Butt doc.”

 

“Rey, how’s going down there?”

 

“I’m very wet and my clit is like a little rock? No signal of orgasms yet.” She heard a strangled moan from him. “Talk dirty to me, doc.”

 

“Is the plug bothering you? Maybe you could change position to touch yourself?”

 

“That isn’t dirty, doc.”

 

“A-are you touching that little greedy clit? I bet you get wet everytime you just think about stuffing your ass like the little piglet you are.”

 

Rey felt a new load of wetness gush towards her asshole, and she begun lightly pinching her clit. Kylo heard her panting, and after a few seconds he added:“ I want to see a picture of your pussy and ass everytime you stretch yourself with a plug. Every fucking time. Do you understand, Rey? So I can imagine my cock filling your little hole and stretching it until it unfurls completely, while your pussy quivers, begging to be touched.”

 

With those words in her ear, Rey finally came, and it was explosive. Her thighs were trembling, and the towel under her butt was soaked. She kept caressing her labia for a little, while her ass was still pulsing around the plug, after her orgasm. She reminded herself to add _exhibitionism_ to her growing kink list.

 

“Rey? Are you there? Did it work? I-I was joking about the pictures, it was just to exci-”

 

“Yes, it worked and no, I didn’t take that order as a joke. I will send pictures starting from the next session. I know you like looking at pussies and, honestly? I want you to look at mine really bad. Goodnight, doc.”

 

-

 

Kylo was almost unable to work the following day. Rey was so bossy and eager and that made him unbelievably hard. He jerked himself after their phone call and another time during his morning shower. He couldn’t believe his luck. He’d never hoped to find another person willing to play with him like that. He couldn’t help feeling proud of her; she was absolutely rocking her training with enthusiasm and attention, and she finally managed to come with something inserted in her. He just hoped she could find someone worthy of her soon, unlike that ex-boyfriend asshole of hers that didn’t even ate pussy.

 

He didn’t receive anything from Rey for two days, and when she messaged him, he almost dropped the phone.

 

_R: My flatmate invited me to a dinner with his colleagues but they’re boring. Can I go with a plug or is it too much time? Your book doesn’t mention boring dinners.”_

 

_K: Yes you can, maybe bring some wet wipes with you if you get uncomfortable and don’t hesitate to remove the plug in the bathroom. Just be careful if it’s a public restroom!”_

 

_R: I need one of your lecherous messages, can you send me one?_

 

Kylo smiled and began recording himself:

 

“Remember that you can’t leave your house with an empty ass. Think about what all the people around you would think if they knew you stretch your asshole every day. And that tonight is no exception. Remember I want to see your pretty pussy after this dinner. Have fun.”

 

After almost three hours, he got a picture and his jaw almost dislodged itself: it was presumably Rey’s pussy, all puffy and wet, with the medium sized plug peeking from under her labia, with the caption:

 

_R: Just finished trembling after great orgasm. Dinner sucked but kept moving the plug with Kegels. Walking plugged is funny. Maybe will take a little break next day. Have a tired pussy in the meantime, I know you love them! :*_

 

He didn’t manage to convey his emotions in a simple written text, so he sent a voice message:

 

“Rey, t-thank you for the picture. You’re beautiful and precious and I’m not sure what I did to deserve this. Good night.”

 

The following week,It was Kylo’s turn to undergo a work dinner. He almost thought about plugging his ass for fun and writing Rey about it but an emergency at the E.R. kept him from returning home, so he went to the restaurant straight from the hospital. His colleagues were chatting about cars and how boring their lives were, so he took his phone in hand, thinking about writing her, but Rey beat him to it.

 

_R: Do you say GIF or JIF?_

 

_K: I’m afraid I’m playing in the JIF team... May I ask why?_

 

_R: You’re really predictable. I’ve learned to make gifs, just wait and see!_

 

He waited, and then a new message arrived: an animated gif where Rey slowly inserted the fourth plug of the set in her asshole after putting it in her pussy to collect moisture, followed by the caption, _Look how smoothly it enters now_. He was finally able to see her butthole stretching around the intrusion, even if the gif wasn’t the highest quality and her skin was almost glowing while her labia bordered on fluorescent pink. He immediately got hard and failed to choke back a gasp. One of his colleagues almost caught him.

 

“Are you okay, Solo? The roast is a little dry, pity they changed the chef last month!”

 

“I’m o-okay,” he said, taking a sip from his glass.

 

He excused himself and walked to a balcony.

 

_K: Rey, I’m at a dinner! Stop sending stuff or I will come in my pants like an idiot!_

 

_R: You’re boring and bourgeoise._

 

And after that, a new gif with her exposing her hard clit and playing with it, plug still in. The caption said: _Until a month ago I would have died of embarrassment thinking about showing my pussy to someone like this and how I get wet just thinking about it! Whose fault is it?_

 

Kylo ran to the restroom and took himself in hand after bolting the door. Not bothering to type a message, he sent a vocal instead:

 

“R-rey I’m alone at least, please!”

 

She replied quickly: the last gif was of her from behind, making the plug bounce lightly and finally expelling it on a towel, captioned with _Look what a good girl, pooping her plug for you._ While her empty hole fluttered, Kylo came so hard that he almost painted the restroom door.

 

_R: Still alive, old man? Enjoyed the show? :)_

 

_K: Keep up the good work, little one, and I will be dead before you’ll manage to use the last plug :Q_

 

But he didn’t die. Rey finally managed to use the plug number six, after almost two months of training. In the meantime, he started using his own set again. He also took pictures of his ass from time to time, to counterbalance her continuous pussy attack.

 

_R: Thanks Doc! Beautiful plug! I imagined you kinda hairier… where’s the cock? ;P_

 

_K: Dick pics are for uncultured swines. And this plug is a special model, designed to press on the prostate. Everytime I clench my butt, my cock leaks precum._

 

_R: I want to seee it_

 

_K: Too old to make gifs, so sorry ;)_

 

They kept indulging in playful banter for another week. Listening to her and looking at her pictures was quickly becoming one of the highlights of his days. His appetite was renewed and he almost felt a teenager again. He started to hug a cushion (even if it was a bit pathetic) while sleeping, dreaming about finally making Rey come with his cock in her. He smiled everytime he thought about her and how sweetly she greeted him every morning, with a pussy picture. He was so happy that he started plugging himself daily again, like when he was freshly married.

 

But he absolutely wasn’t ready when she finally requested to meet him in person.

 

_R: I’m using the biggest plug since last sunday, do you think I’m ready for the real deal?_

 

_K: Sorry? Do you need a bigger one?_

 

_R: The real deal would be your cock, silly. Fuck my ass, pretty please. I feel ready._

 

After sending the last message, she received a phone call from him.

 

“Doc?”

 

“Rey, you don’t know what you’re asking. Meeting in person would not be appropriate and-”

 

“May I ask you why? We’re both adults and we live in the same town? Meeting doesn’t seem anyth-”

 

“P-please listen, Rey. We’re technically two strangers and I’m too old for yo-”

 

“Would you cut the crap? We talked everyday for two months now, you’re a bit older but nothing dramatic and I don’t want to lose my anal virginity with a crusty boy that could possibly injure me! You’re the only butt expert I know and I would like to try your cock, thank you very much! I trained my asshole for two months for that cock, did you forget that?”

 

Kylo was speechless. But she had a point: when in need of surgery, do you want to be operated by the best surgeon around or you just ask a first year student? In Rey’s case, letting someone else fuck her first-class ass would have been like getting brain surgery from a scarecrow with its eyes pecked out by birds.  

 

Just to cockblock himself, he blurted out:

 

“I will send you a picture of my face, and if you still want me to fuck you after seeing it, we’ll do it as soon as possible. Have a nice day, Rey.” He ended the call.

 

He was absolutely sure that Rey would back out after seeing his nose, his ears and his scar. No need to worry about fucking hot young girls in the ass anymore. Very young and very hot. He’d never seen Rey’s face but her pussy was the fuel of pure raunchy dreams. Whatever.

 

The following day, he decided to finally take a picture. He gathered his hair in a half bun to better expose his ears, and he put on his black rimmed glasses because hot young girls surely couldn’t like old anal-addicted sickos with glasses. He took a selfie trying to seem serious and unforgiving and he sent it to her before shitting his pants and backing out.

 

She didn’t reply after a minute, nor two, nor ten, and he surely wasn’t checking his phone every thirty seconds to see if she’d answered. After an hour, he just sighed and put the phone away.

 

He’d managed to scare her. He was assaulted by a sudden sadness and his good old insecurities came back to haunt him from his high school years.

 

“Great job Ben, you are the worst idiot on earth.”

 

He called the hospital saying that he wasn’t feeling well and he was going to stay home for a few days. His house needed some attention anyways, maybe working with his hands could help him not to think about the greatest opportunity of his life butchered by his ugly mug.

 

Bollocks. He cried mowing the lawn, and again cleaning the windows. He didn’t cry cutting wood just because there was an axe in his hands and it could be dangerous. But he cried again afterwards, while drinking tea. He wasn’t just crying because he wasn’t going to fuck the hottest butt of the century, he was crying because he felt he lost Rey’s friendship too.

He would have been the happiest man on earth if he could just continue chatting with her and exchange jokes, even without the whole butt situation. But she never answered after he sent his damned selfie.

 

That night he decided to torture himself and, instead of sleeping, he read all their emails and their messages. He decided to finally close his eyes while the sun was rising, after seeing again the last pic she sent, just three days before: she was keeping her pussy spread with her fingers, and there was a pink rosebud inserted in her ass.

 

A fucking rosebud. No one inserted flowers in their ass for him before, not even that stupid Hux, who liked to stuff his butt with the strangest things. The caption said: _Good Morning! XOXO Rey_

 

He was madly in love with her.

 

“Good morning indeed,” he told the rosebud, and then covered his face with a cushion, finally falling asleep.

 

His phone woke him around mid-day. He took it from the side table and almost dropped it when he saw that there were several messages from Rey. He squinted his eyes and he saw that her messages contained pictures of some kind of document. He phoned her right away. She seemed very cheerful.

 

“Hey!”

 

“Rey, what did you just send me?”

 

“Were you sleeping? Your voice is so sleepy! I bet you’re the cutest patootie right now!”

 

Ben wasn’t sure to have heard correctly.

 

“What? Rey?”

 

“I just sent you my blood test, silly. I want to go bareback if you’re clean. I’m tired of putting plastic in my ass, I want to feel you. Are you clean?”

 

Again, he was sure he couldn’t have have heard correctly. He wasn’t even sure he was even alive at this point. She’d finally managed to kill him. Or not: his cock was rock hard.

 

“H-how are you not disgusted?” he managed to croak. “You’ve seen my face and you still want me to put my penis in your anus.”

 

“Why should I be disgusted? You’re lovely, and I can’t wait to be plundered by your bare cock while you watch me with that piercing eyes of yours.”

 

“Fuck Rey, fuck! I’m clean, when can I fuck you? I’m free until Sunday, took some days off. I’m ready to come to you right now if you want!” His heart was beating wildly and he was fully awake now.

 

“Whoa, easy there! My flatmate will go on a short trip with his girl on Saturday morning; you can come here right after they leave the house. I’ll send you more details tomorrow. Can’t wait to meet you, Kylo, you have no idea.”

 

After she closed the call, he begun palming his cock, still unbelievably hard from before. He really couldn’t believe his luck: Rey had begged to be fucked, seen his face, and then begged to be fucked without a condom.

 

About to explode, he wet his middle finger with his tongue and pushed it past his butthole: he found his prostate right away and pushed hard against it, coming on his chest and chanting Rey’s name.

 

Slightly more sober after a cup of coffee, he contacted her again:

 

_K: I would like you to tell your friends that I’m coming to your house on Saturday. I’m about to send you a picture of my ID with my full name and address. Send everything to them, please. You should also tell them that we’re going to have sex, just in case something goes wrong.”_

 

_R: I will send them your ID but I’m not going to tell them what we’ll do! I may be an exhibitionist at heart, but this may be too much?”_

 

_K: Okay. We should also decide for a safeword. Choose it. I want you to know that you can change your mind whenever you want, you can back off even now if you’re not feeling up to having sex with me. Okay?”_

 

 _R: Ben, don’t fuss too much please. I will keep that in mind, just keep calm! My safeword will be_ desert _. And you will tell me what happened to your beautiful face after you fuck me._

 

He exhaled from his mouth. His cock was hard again. He had a day and half to masturbate in order to not come in his pants before fucking his good girl. He took out his toy collection from under the bed and began preparing himself.

 

Saturday morning came in a heartbeat. He managed to wank six times on Friday, wearing various plugs and even using a vibrator, and he wanked a seventh when Rey sent him new pictures of her freshly shaved pussy.

 

She told him to come over after eleven and he rang her doorbell at 10:59, prim and proper, with a little bag containing some useful items.

 

His heart was about to explode; he was finally going to see Rey’s face. While he was absolutely sure she was beautiful, he still wasn’t convinced she could really find him attractive, even if she repeated multiple times that she loved his nose, moles, and ears while having phone sex the previous day.

 

The door finally opened, and he thought about dying on the spot: Rey was indeed the loveliest girl he’d ever seen. She took him by the ears, sloppily smashing their mouths together. After a few licks, she finally greeted him.

 

“Here you are! I can’t believe you’re finally here to fuck my ass!”

 

“I c-can’t believe I’m here to fuck your ass either! I still think I’m dreaming!”

 

“Nonsense, silly! Let’s do it now, I can’t wait anymore.” She took his hand and went to her room. The rest of the small apartment was a blur; he just followed her while she kept talking:

 

“... wearing number six right now, but this morning I kinda freaked out after pooping so I tried cleaning the insides with water and the outsides with soap and I hope that’s enough anyway can’t wait to show you my pus-” He stopped her, taking her face in his hands.

 

“Rey, stop or you’ll freak out and I will follow. We’re both nervous, I would like you to keep calm and follow my instructions. We can stop right now if you’re not re-”

 

“No! I want to do it,” she whined.

 

“Okay, tell me your safeword. I want to remind you that I will stop completely when you say it.”

 

“Desert. It’s desert,” she told him, watching at him as he poured the content of his little bag on her table.

 

“Good girl. I brought some condoms in case you’ll change idea about barebacking, and my favourite lube. I hope that’s okay. I have wet wipes too. Now I want to do something that will relax you. Do you have suggestions?”

 

“Want you to look at my pussy, please,” she whined again, beginning to undress. He was pretty amused by this exhibitionist side of her.

 

Completely naked, she lay on the bed and opened her legs in front of Ben. He was thrilled: he already knew she was wearing the biggest plug, but seeing that in person was an almost out-of-body experience. She lay mostly still, only moving to open her cunt with her fingers, red as a beet but perfectly calm. Ben approached her, observing her vulva with attention.

 

“Your cunt is a masterpiece and you’re spreading it beautifully for me, but we both know I’m not here to stick my cock in there, right, Rey?”

 

She nodded enthusiastically.

 

“So, unless you need vaginal stimulation to come, I will play a bit with your pretty little clit until you’re coming and then we will move to the main event, is that okay?”

 

Rey nodded again. Ben caressed her soft thighs with his hands and then dove straight for her exposed clit, lapping at it sloppily. It was so engorged that they both moaned loudly, and she jolted when he started sucking lightly.

 

“Keep open… good girl! What we have here?” he said after her pussy gushed a load of moisture.

 

She was moaning wildly and he kept caressing her nub with his right hand, while he began to remove the plug with the other one. After a little resistance, he managed to dislodge it from her butt, observing her rim slowly trying to return to its natural state.

 

He put his tongue there, and Rey cried “Ben!”

 

“You’re so beautifully stretched! You will took my cock like a champion, I’m sure of it,” he said, before lapping enthusiastically at her hole.

 

She was writhing under his attention, and she finally came after he put pressure on her clit, moaning his name.

 

“Rey, are you ok?” he whispered, caressing her thighs. “Are you hurting somewhere or we can keep going? I’d like to fuck you on your table if that’s alright?”

 

Rey was almost delirious but managed to nod nonetheless. Ben brought some cushions over to the table and covered everything with a towel. He then picked up Rey like a doll, cradling her limp body in his arms.

 

“You’re such a good girl, we’re almost there. Let’s check if your little hole is still open?” and he probed her with his fingertips, kissing sweetly her forehead.

 

“Yes it is! Your greedy little hole is all sloppy and pliant and I’m finally going to stick my cock in it! Aren’t you happy?”

 

Rey nodded again, but after he deposited her on the table and took a moment to clean his hands with a wet wipe, she whispered: “Don’t you want me to suck your cock?”

 

“Now Rey, don’t be silly,” he answered, caressing her inner labia to wet his fingers “You have trained so hard to be here today that sucking my dick would be a waste.” He plundered her hole with one, then two, and finally three fingers. “You trained so hard that you managed to take three of my fingers up your ass without any fuss. I think I’ll reward you with my cock now.”

 

Rey released a broken moan: “C-can I at least see it?”

 

“You will see it after I fuck you. Not before and that’s not negotiable. Now be a good girl and keep your legs spread open for me.”

 

She just complied, folding her knees toward her chest. In the meanwhile, he wiped his hands again, put another cushion under her ass and reminded her of her safeword. He then ordered her to close her eyes while he disrobed and lubed up his cock.

 

“Good girl. I’m going to insert the tip of my penis in your little hole now, then I will stop for a moment to see if you’re okay. I want you to keep your eyes closed for a little more, and I want you to push against me. Is that okay?”

 

Rey nodded, visibly trembling. He lined his tip with her and pushed inside until her rim swallowed the head of his cock, closing around its ridge. Rey’s body was covered in goosebumps and they both exhaled at the same time.

 

“Good girl, you’re so good, Rey, you have no idea. Did I hurt you?”

 

She shook her head. It hurt a little, but it was already gone.

 

“That’s great news! If you feel okay, let’s plunder that little hole of yours, what do you think?”

 

She nodded enthusiastically again.

 

“I want you to count until three. At three, you will push again against me, and I want you to open your eyes while I penetrate you, and look at me. Is that ok?”

 

Rey didn’t nod but started counting right away: “One.”

 

Ben’s heart was never so full of love and admiration as in that moment.

 

“Two.”

 

He was completely besotted. He would have killed for her.

 

“Three.”

 

At three, several things happened at once: she finally opened her eyes and was almost blinded by the never ending expanse of skin in front of her; Ben slowly and firmly pushed his cock inside her (luckily she remembered to push too), bottoming out; Rey’s mouth opened and she let go a surprised and delighted “Oh!”, before finally latching her eyes with Ben’s.

 

She would never forget this sensation. “Being full” was just a stupid euphemism for prudish girls, she literally felt impaled. She could clearly discern the tip of his cock inside her and her rim stretched like an elastic band about to snap around his girth. Feeling him breach her virgin ass was both the most wrong and the most right sensation of her life and she’d never felt so aroused.

 

He was still watching her, and his eyes were shining in awe.

 

“I want you to know that I never felt more proud in my life, even if you decide right now to safeword, you’re the most brave and beautiful woman I ever met. Now, if you want to continue, I will keep still for a minute or two in order to let your ass getting used to my presence. Is that okay?”

 

“What will we do in the meantime?”

 

“Oh, I have no idea” he said, caressing her inner lips with both pointers “you could begin calling me Ben for one, I think you’ve earned it.”

 

He then chuckled and pinched her nipples with his wet fingers, until they puckered. Rey moaned, bewildered by the feeling. She never played with her nipples, but the cock in her ass was heightening every sensation so far.

 

“You could release your legs and lend me a hand, what do you think? Spread your outer labia, I want to see your clit poking out, without hindrances.”

 

Her face became crimson but she complied, releasing her legs that fell even more open; she spread her pussy, looking him defiantly in the eyes.

 

“I want to take a picture, I never saw something so outstanding,” he said, reaching for his phone that sadly remained in his pants, on the ground.

 

“Take mine, it’s in the drawer.”

 

He opened said drawer and took her phone. On the side, there was the brown envelope he used to bring her his book, carefully folded. There was her name on it, written by him. He exhaled, taking a few seconds to compose himself again.

 

He took the picture and showed her. She felt like she was floating. His cock was not small at all, and she would have definitely freaked out seeing it before taking it in her. Her pussy started gushing and he took advantage of that, wetting his fingertips and pinching her clit and nipples again and again.

 

She released her labia, whining: “Please Ben, I can’t take it anymore!”

 

“Do you want to safeword?” he said, rubbing her clit steadily.

 

“I want you to move that damn cock!”

 

And he did. Rey cried, “Thank you! Thank you!”

 

His movements were slow and steady, reaming her asshole and massaging her clit at the same time. He was mesmerized by the movement of her rim, pulled in and out by his cock.

 

“You know Rey, usually lube needs to be reapplied more than once, but your beautiful pussy is doing all the work here. There’s a steady flow finishing right on my cock, did you know? I think you’ll get a reward for that” he said, changing his angle of penetration and attacking the thin wall between her anus and her vagina with shallow and rapid thrusts.

 

Rey began moaning loudly and finally convulsed when he put pressure on her clit, squashing it with his thumb. They both felt clearly her ass clenching around his girth and he finally came too, spurting deep inside of her.

 

“I have no words Rey, no words,” he whispered, folding himself down to kiss her face sweetly.

 

She squealed, her whole body tingling: “I can’t believe we did it for real! Can we do it again?”

 

Ben’s breath stuttered. Not only she loved having her ass fucked by him, but she wanted to do it again.

 

He was doomed.

 

He helped her down the table and, still smooching her face, he accompanied her to the bathroom.

 

They took a long bath together and spent the rest of the day chatting and cuddling like lovesick teenagers. She demanded repeatedly to be fucked again, but she soon realized that her ass was still a bit tender. After dinner he ate her out on the sofa and she came twice.

 

She wanted to suck his cock really badly but she fell asleep after his ministrations, so he tucked her into bed and returned home. He couldn't help thinking that Rey would change her mind about him, his insecurity returning after that wonderful day with her.

 

But the following morning, he was greeted by the customary pussy pic, with the caption: _She’s sad you left her ;_;_

 

He smiled, his heart soaring.

  


After three days, Rey’s doorbell rang insistently. She wasn’t expecting anyone, so she was really puzzled when a courier put a package in her hands, made her sign on a tablet and hurried away.

 

She brought the packet inside and inspected it carefully. There wasn’t a name or address on it, save for hers. She put it on the table and tried to unpack it, keeping some distance, just in case.

 

She finally managed to breach it with a long knife, and saw a black case inside, very similar to her plug set case. She finally opened it completely, and immediately knew who sent the parcel: it was a beautiful strap-on silicone dildo, with real leather straps. She opened the card that was in the box with the toy. It wasn't handwritten, but she enjoyed it nonetheless.

 

_Are you free this weekend? I would like to teach you something new._

_Love, Ben_

 

She grinned, feeling whole.

 

 

 

 

 

 

 

 

 

 

**Author's Note:**

> You can launch vegetables at my head at persimonne.tumblr.com


End file.
